Benzoyl chloride → Methyl N-benzoyl-3-amino-3-(3,4-dimethoxyphenyl)propionate

HRID 1003601Notes

Reaction equation

HRID 1003601 reaction equation
Cl.[NH2:2][CH:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[CH2:4][C:5]([O:7][CH3:8])=[O:6].C(N(CC)CC)C.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>O1CCCC1>[C:26]([NH:2][CH:3]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[CH2:4][C:5]([O:7][CH3:8])=[O:6])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 16277031Methyl 3-amino-3-(3,4-dimethoxyphenyl)propanoate hydrochloride

Product 1

HCID 9949978Methyl N-benzoyl-3-amino-3-(3,4-dimethoxyphenyl)propionateYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice bath cooled stirred suspension of methyl 3-amino-3-(3,4-dimethoxyphenyl)propionate hydrochloride (0.689 grams, 2.50 mmol) and triethylamine (0.7 milliliters, 5 mmol) in 15 milliliters of tetrahydrofuran was added 0.3 milliliters of benzoyl chloride (2.6 mmol). The cooling bath was removed after 15 minutes and the mixture stirred for an additional 45 minutes. The reaction mixture was then diluted with 15 milliliters of brine and 15 milliliters of water and then partially concentrated in vacuo to remove the tetrahydrofuran. The reaction slurry was filtered, the solid air-dried, then dried in vacuo (60° C., <1 mm) to afford 0.86 g (100%) of the product as a white powder: 1H NMR (dmso-d6, 250 MHz) δ 8.84 (d, J=8.3 Hz, 1 H, NH), 7.83 (m, 2 H, Ar), 7.60-7.35 (m, 3 H, Ar), 7.06 (s, 1 H, Ar), 6.90 (m, 2 H, Ar), 5.50-5.30 (m, 1 H, CHN), 3.75 (s, 3 H, OCH3), 3.72 (s, 3 H, OCH3), 3.46 (s, 3 H, CO2CH3), 3.05-2.75 (m, 2 H, CH,); 13C NMR (dmso-d6) δ 17 165.6, 148.6, 147.9, 134.9, 134.5, 131.2, 128.3, 127.3, 118.5, 111.6, 110.6, 55.5, 55.5, 51.4, 49.7, 40.6. Anal. Calcd for C19H21,NO5. Theoretical C, 66.46; H, 6.16; N, 4.08. Found C, 66.22; H, 6.05; N, 3.98.

Workup

  1. temperatureTo an ice bath cooled
  2. customThe cooling bath was removed after 15 minutes
  3. stirringthe mixture stirred for an additional 45 minutes
  4. additionThe reaction mixture was then diluted with 15 milliliters of brine and 15 milliliters of water
  5. concentrationpartially concentrated in vacuo
  6. customto remove the tetrahydrofuran
  7. filtrationThe reaction slurry was filtered
  8. customthe solid air-dried
  9. customdried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-dccc0eda7d7849b68a31676568ec4881
Source dataset
uspto-grants-2000_04
Patent number
US06046221

Reaction notes

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